18423-69-3
Chemical Structure
Cubebin
Synonym(s): (-)-Cubebin
- CAS No.: 18423-69-3
- Formula:C20H20O6
- Molecular Weight:356.37
IUPAC Name: 2,2-difluoro-2-(1,4-dioxaspiro[4.5]decan-8-yl)ethan-1-amine
InChIKey: DIYWRNLYKJKHAM-MDOVXXIYSA-N
SMILES: O[C@@H]1[C@@H]([C@H](CO1)CC2=CC=C3C(OCO3)=C2)CC4=CC=C5C(OCO5)=C4
Biological Activity: Cubebin ((-)-Cubebin), a dibenzyl butyrolactone lignan, is an orally active AChE inhibitor. Cubebin binds to active sites of NF-κB, TNF-α, and TGF-β1 via hydrogen and hydrophobic interactions, obstructing critical residues to inhibit pro-inflammatory or renal fibrosis-related activity. Cubebin enhances p38 MAPK phosphorylation to increase tyrosinase gene expression, stimulating melanogenesis via elevated tyrosinase activity, expression, and mRNA levels. Cubebin reduces oxidative stress via enhanced endogenous antioxidant enzyme activity and inhibited lipid peroxidation, regulates lipid metabolism, improves glycemic control, and exerts renoprotective effects via reduced renal dysfunction markers and improved renal architecture. Cubebin shows antimicrobial activity. Cubebin exerts larvicidal activity against Angiostrongylus cantonensis larvae, with no cytotoxicity toward monkey or human cell lines or Caenorhabditis elegans. Cubebin can be used for the research of diabetic nephropathy, melanoma, colon adenocarcinoma, neuroangiostrongyliasis, Alzheimer’s disease (AD) and depression[1][2][3][4][5][6][7].
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Cubebin | Cubebin ((-)-Cubebin), a dibenzyl butyrolactone lignan, is an orally active AChE inhibitor. Cubebin binds to active sites of NF-κB, TNF-α, and TGF-β1 via hydrogen and hydrophobic interactions, obstructing critical residues to inhibit pro-inflammatory or renal fibrosis-related activity. Cubebin enhances p38 MAPK phosphorylation to increase tyrosinase gene expression, stimulating melanogenesis via elevated tyrosinase activity, expression, and mRNA levels. Cubebin reduces oxidative stress via enhanced endogenous antioxidant enzyme activity and inhibited lipid peroxidation, regulates lipid metabolism, improves glycemic control, and exerts renoprotective effects via reduced renal dysfunction markers and improved renal architecture. Cubebin shows antimicrobial activity. Cubebin exerts larvicidal activity against Angiostrongylus cantonensis larvae, with no cytotoxicity toward monkey or human cell lines or Caenorhabditis elegans. Cubebin can be used for the research of diabetic nephropathy, melanoma, colon adenocarcinoma, neuroangiostrongyliasis, Alzheimer’s disease (AD) and depression. | |||||||||||||||||||||
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- [1]. Syed RU, et al. Effect of cubebin against streptozotocin-induced diabetic nephropathy rats via inhibition TNF-α/NF-κB/TGF-β: in vivo and in silico study. Sci Rep. 2025;15(1):4369. Published 2025 Feb 5. [Content Brief]
- [2]. Bastos JK, et al. Anti-inflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo Griseb. J Ethnopharmacol. 2001;75(2-3):279-282. [Content Brief]
- [3]. Hirata N, et al. Mechanism of the melanogenesis stimulation activity of (-)-cubebin in murine B16 melanoma cells. Bioorg Med Chem. 2007;15(14):4897-4902. [Content Brief]
- [4]. Niwa AM, et al. Evaluation of lignan (-)-cubebin extracted from Piper cubeba on human colon adenocarcinoma cells (HT29). J Toxicol Environ Health A. 2016;79(2):92-100. [Content Brief]
- [5]. eixeira TR, et al. Cubebin, a Lignan Isolated from Drimys andina, Exhibits Potent and Selective Antiparasitic Activity against Angiostrongylus cantonensis. ACS Omega. 2025 Jul 11;10(28):31161-31169. [Content Brief]
- [6]. Wan M, et al. Cubebin alleviates chronic stress-induced depression-like behavior in mice by regulating the gut microbiome. Eur J Pharmacol. 2025;994:177384. [Content Brief]
- [7]. Patil, S., et al. (2025). Cubebin and Its Derivatives in Neurodegenerative Diseases and Their Antimicrobial Potential. In: Mukherjee, B. (eds) Dietary Supplements and Nutraceuticals.
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